Month: March 2021

Reference of 4316-42-1, A common heterocyclic compound, 4316-42-1, name is 1-Butyl-1H-imidazole, molecular formula is C7H12N2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1-butyl imidazole put 1.82 mmol (0.24 mL) and 2.18 mmol NH4I (317 mg) and trimethyl ortho formate 9.1mmol (1 mL) in a Schlenk reaction tube and reflux under air or N2. Confirming that the protonated imidazole disappears then removed trimethyl ortho formate remaining under vacuum, and then, a small amount of the protonated imidazole deprotonation was passed through a basic alumina dissolved in ethyl acetate. After having passed through this solution, putting them in a vacuum and the product was confirmed by NMR. Yield: 98%

The synthetic route of 4316-42-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pusan National UniversityIndustry-AcademicCooperation Foundation; Park, Jin Gyun; Kim, Do Chung; Oh, Gyung Hwan; (23 pag.)KR2015/79403; (2015); A;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthetic Route of 33468-69-8, These common heterocyclic compound, 33468-69-8, name is 4-(Trifluoromethyl)-1H-imidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

l-10h) 4-(trifluoromethyl)-1 /-/-imidazole (Flourine Chemicals, Shanghai, China) (291 mg) was stirred in 20 ml_ anhydrous THF at room temperature under nitrogen. A lithium bis(trimethylsilyl)amide solution (1.96 ml_ , 1.0 M in THF) was added. After 50 minutes, a solution of intermediate (l-10g) (685 mg) in 10 ml_ anhydrous THF was added. The reaction was stirred for 2 hours. The reaction was quenched with saturated ammonium chloride and diluted with brine and ethyl acetate. The aqueous layer was extracted, dried, filtered, and then concentrated. The resulting residue was purified (Combi-flash, Redi-sep 40 g, 30% ethyl acetate/heptane gradient to 100% ethyl acetate/heptane) to afford (l-10h): m/z 307.4 (M+H)+.

The synthetic route of 33468-69-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; BENBOW, John William; LOU, Jihong; PFEFFERKORN, Jeffrey Allen; TU, Meihua Mike; WO2010/29461; (2010); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 583-39-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 583-39-1 as follows.

General procedure: A mixture of 0.001 mol of chloroethynylphosphonate1a-1c and 0.002 mol of benzimidazole-2-thione 2d in 15 mL of anhydrous acetonitrile was stirred at room temperature for 2-5 h. The precipitate was filtered off. The solvent was removed from the filtrate, the precipitate was combined and recrystallizedfrom ethanol. Yields and melting points of the obtained compounds are given in Table 1.

According to the analysis of related databases, 583-39-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Egorov; Piterskaya, Yu. L.; Kartsev; Polukeev; Krivchun; Dogadina; Russian Journal of General Chemistry; vol. 88; 9; (2018); p. 1824 – 1831; Zh. Obshch. Khim.; vol. 88; 9; (2018); p. 1478 – 1485,8;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 641571-11-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 641571-11-1, name is 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

A suspension of 1 (0.10 g, 0.40 mmol), 51 (0.13 g, 0.54 mmol), Pd2(dba)3 (25 mg, 0.027 mmol), t-tert-buty phosphine (IM in toluene; 0.1 mL, 0.10 mmol) and potassium tert- butoxide (0.25 g, 2.2 mmol) in dioxane/DMF (1/1; 6 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 0C for 30 min. After cooling to room temperature, the resulting mixture was filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (20 mL). The combined aqueous layers were extracted withEtOAc (2 x 20 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue re-dissolved in minimum amount of EtOAc and hexanes added until solid precipitated. After filtration, the title compound was obtained as a light brown solid (23 mg, 13%).[0264] 1K NMR (500 MHz, DMSO-J6): delta 2.20 (s, 3H), 2.33 (s, 3H), 6.93 (dd, J = 3.6, 1.7 Hz, IH), 7.41 (dd, J = 3.6, 2.3 Hz, IH), 7.44 (s, 2H), 7.50 (s, IH), 7.97 (s, IH), 8.20 (d, J = 0.8 Hz, IH), 8.27 (s, IH), 8.46 (s, IH), 11.84 (s, IH)MS (ES+): m/z 455 (M+H)+

The synthetic route of 3-(4-Methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN INC.; WO2009/49028; (2009); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 1003-21-0,Some common heterocyclic compound, 1003-21-0, name is 5-Bromo-1-methyl-1H-imidazole, molecular formula is C4H5BrN2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a flask containing 5-bromo-1-methyl-1H-imidazole (650 mg, 4.04 mmol) was added THF (10 mL) and the clear homogeneous solution was stirred at room temperature as iPrMgCl (2 M in diethylether, 2 mL, 4 mmol) was added. A whitish suspension resulted. The suspension was stirred at room temperature for 30 minutes, then a solution of 4-chloro-2-methoxy-3-(4-(trifluoromethyl)benzyl)quinolin-6-yl)(2,6-dimethylpyridin-3-yl)methanone (660 mg, 1.36 mmol, Intermediate 81: step b) in THF (5 mL) containing LaCl3-LiCl complex (0.5 M solution THF, 5 mL, 2.5 mmol) was added to the reaction mixture. The reaction mixture was stirred overnight at 35 C. After 14 hours, the reaction mixture was quenched with saturated aqueous NH4Cl solution. The aqueous portion was extracted with EtOAc (3*40 mL) and the combined organics were washed with brine and dried over MgSO4. The brine portion was back-extracted with DCM (3*40 mL) and dried over MgSO4. The organics were filtered and concentrated to dryness to afford a tan oil. The residue was purified by FCC (2% MeOH-DCM increasing to 10% MeOH) to provide the title compound as an off white solid. 1H NMR (500 MHz, CDCl3) delta 8.13 (d, J=2.0 Hz, 1H), 7.76 (d, J=8.7 Hz, 1H), 7.50 (d, J=8.2 Hz, 2H), 7.44-7.35 (m, 4H), 7.31 (d, J=11.4 Hz, 1H), 7.05 (d, J=8.0 Hz, 1H), 6.90 (d, J=8.0 Hz, 1H), 6.19 (s, 1H), 4.67 (s, 1H), 4.32 (s, 2H), 4.07 (s, 3H), 3.46 (s, 3H), 2.52 (s, 3H), 2.45-2.33 (m, 3H); MS (ESI): mass calcd. Chemical Formula: C30H26ClF3N4O2, Exact Mass: 566.2. m/z found 567.1 [M+H]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1-methyl-1H-imidazole, its application will become more common.

Reference:
Patent; Janssen Pharmaceutica NV; Leonard, Kristi A.; Barbay, Kent; Edwards, James P.; Kreutter, Kevin D.; Kummer, David A.; Maharoof, Umar; Nishimura, Rachel; Urbanski, Maud; Venkatesan, Hariharan; Wang, Aihua; Wolin, Ronald L.; Woods, Craig R.; Fourie, Anne; Xue, Xiaohua; Cummings, Maxwell D.; Jones, William Moore; Goldberg, Steven; US2015/105366; (2015); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of 13750-62-4,Some common heterocyclic compound, 13750-62-4, name is 1-Benzyl-2-methyl-1H-imidazole, molecular formula is C11H12N2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 1-Benzyl-2-methylimidazole (0.32 cm3, ?2 mmol) was dissolved in acetonitrile (10 cm3) and then slowly added to warm solution of PdCl2 (0.18 g, 1 mmol) (in the synthesis of thiocyanate complex the NH4SCN (0.15 g, 2 mmol) was added) in acetonitrile (30 cm3). The mixture was refluxed for about 2 h and after the time the reaction solution was filtered and yellow single crystals were obtained by slow evaporation of the solvent. Yield: 88% for chloride complex (1) and 92% for thiocyanate analog (2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Benzyl-2-methyl-1H-imidazole, its application will become more common.

Reference:
Article; Ma?ecki; Maro?; Polyhedron; vol. 50; 1; (2013); p. 452 – 460;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Related Products of 53710-78-4, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 53710-78-4, name is 1-(3-Chloropropyl)-1H-imidazole belongs to imidazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 60% NaH (9.6mg, 0.24mmol) was added to a solution of 5a (100mg, 0.24mmol) in dry DMF (10mL) at room temperature. After stirring for 30min, 1-(3-chloropropyl)-1H-imidazole (52mg, 0.36mmol) was added and the mixture was then stirred for 5h at 80C. After cooling, the mixture was poured into cold water (200mL) and extracted with EtOAc (3¡Á50mL). The combined organic phase was washed with brine (3¡Á150mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using dichloromethane/ 20 methanol/triethylamine (120:4:1, v/v/v) as eluent to afford 64.4mg (51.0%) 6a as a red solid.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1-(3-Chloropropyl)-1H-imidazole, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Liu, Xiaoqi; Hu, Yuanyuan; Gao, Anhui; Xu, Meng; Gao, Lixin; Xu, Lei; Zhou, Yubo; Gao, Jianrong; Ye, Qing; Li, Jia; Bioorganic and Medicinal Chemistry; vol. 27; 4; (2019); p. 589 – 603;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 104619-51-4, These common heterocyclic compound, 104619-51-4, name is Di(1H-imidazol-1-yl)methanimine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To 4-[3-tert-Butylsulfanyl-2-(2,2-dimethyl-propyl)-5-(pyridin-2-ylmethoxy)-indol-l- ylmethylj-benzoic acid hydrazide (0.05g, O. lOmmol) in DMF (lmL) was added C-(Di-imidazol-l- yl)-methyleneamine (0.08g, 0.50mmol), and the reaction was heated at 85C for 3 hours. The mixture was cooled to room temperature and partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgS04, filtered, and concentrated. The residue was purified on silica gel (EtOAc:hexane gradient) to give the desired product.

The synthetic route of 104619-51-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AUTOIMMUNE PHARMA LLC; BENISON, Jeffrey; (157 pag.)WO2018/152405; (2018); A1;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of 934-22-5, These common heterocyclic compound, 934-22-5, name is 6-Aminobenzimidazole, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: HATU (60 mg, 0.16 mmol) was added to a solution of DIPEA(0.069 ml, 0.39 mmol), 1H-indazole-5-amine (26 mg, 0.2 mmol) and 9a(33 mg, 0.13 mmol) in DMF (5 ml) at room temperature. The mixturewas stirred at room temperature overnight. The reaction was quenchedwith sat. aq. NaHCO3 at room temperature and extracted with AcOEt.The organic layer was separated, washed with water and sat. aq. NaCl,passed through a pad of NH silica gel (eluent: AcOEt). The residue waswashed with AcOEt to afford 1c (33 mg, 68%) as a white solid.

The synthetic route of 934-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mizojiri, Ryo; Nii, Noriyuki; Asano, Moriteru; Sasaki, Masako; Satoh, Yoshihiko; Yamamoto, Yukiko; Sumi, Hiroyuki; Maezaki, Hironobu; Bioorganic and Medicinal Chemistry; vol. 27; 12; (2019); p. 2521 – 2530;,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Application of 96797-15-8, A common heterocyclic compound, 96797-15-8, name is 4-Iodo-1-trityl-1H-imidazole, molecular formula is C22H17IN2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: 4-Iodo-1-trityl-1H-imidazole (5, 2 g, 4.58 mmol), (5-chloro-2-methoxyphenyl)boronic acid(0.852 g, 4.58 mmol), K3PO4 (2.9 g, 13.7 mmol), Pd(PPh3)4 (0.74 g, 0.64 mmol) were added todry dimethylformamide (30 mL). The reaction mixture was stirred at 100 C under inert atmosphere,until the starting material disappeared in TLC. The reaction mixture was distilled in vacuo, and ethylacetate (100 mL) was added to the mixture. The organic extract was washed twice with saturatedaqueous NaCl (20 mL), and the organic extract was dried over Na2SO4. After solvent was removedunder vacuum, the product was purified as a white solid by silica gel column chromatography, 1.2 g,yield 63%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Wen, Hui; Liu, Yuke; Wang, Shufang; Wang, Ting; Zhang, Gang; Chen, Xiaoguang; Li, Yan; Cui, Huaqing; Lai, Fangfang; Sheng, Li; Molecules; vol. 24; 11; (2019);,
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem